The Ann & Winston Show
by Winnie-the-Bish
Summary: The Ann & Winston Show! Ann and Winston are two strangers who decide to move to New York City together after meeting on a plane and commiserating over their unfulfilling lives. Featuring Doctor Sam as Ann's charming and handsome coworker.
1. Chapter 1: Flight

It was a cold windy day in the beautiful bright city of Chicago where anything could happen. Winston walked into the O'hare was wearing a dark green jacket that looked like it was not good enough to keep him warm in this time of year and had a small carry-on backpack. After getting his luggage checked, going through security,and grabbing a bite to eat he finally sat down in the seating area of his terminal. Time went pass. It felt like forever. Finally, the announcer called for all people going to New York to line up. Winston made his way in the line,but it already got crowded by the time he got there. When he got to the front a short, blond haired lady asked him for his ticket. Reaching through his pocket removing the ticket.

"Now I know that you've never seen a fine black man such as myself get on a plane,but let me tell you something when you got money like me, Baby you best to believe I'm the man." Winston said with too much pride. The lady looked up at him with a dull face and started shaking her head. Winston took that as offense.

"Oh I see you can't be happy for a brotha".

"Sir, your flying coach. It's nothing to get excited over." She gave him a smug look after she ranged the ticket. " Thank you sir for choosing O'hare as your #1 airport service." As Winston started walking he turned and said " No It is me who should be thanking you, because I could have chose SouthWest."

"Um sir, I think you mean MidWay airport because SouthWest is an airline. Now if you don't mind I have other people to tend to". Then she snapped her head around to attend to the next passenger. Winston turned on his heels and walked down the ramp. When he got into the plane a flight attendant lead him to his seat. There his sat next to the the window seat. He put his bag into in between his legs. Scrabbling in his bag and pulling out a pair of headphones and his phone. He raised the windshield and looked out of it. clearing his mind on what his next move would be in "The Big Apple".

"Wait, wait,wait. I'm here don't close the gate." A woman called as she was making her way towards the gate. Her hair was all over the place. She was breathing hard and looked very disheveled. Taking the ticket out of her purse and handing it to the lady.

"Well it's not like we were waiting for you." the lady said under her breath,but loud enough for the woman to here. "Excuse me, did you want to be more clear." with a more heavier tone. The lady scanned the ticket and waved her towards the ramp. The woman made her way on the plane. One of the flight attendant guided her towards her seat. When she got there someone was already in her row. she thanked the flight attendant and scooted into the seat right next to the man.

He felt someone brush a hand on his thigh,so he turned his head from the window to pay his full attention next to him. "Oh I'm so sorry; just trying to get seated." she said while getting comfortable in her seat. Winston took of his headphone out slowly placing them on his lap. He started at the her. She was a brunette, with dark peach skin, beautiful hazel green eyes, and small freckles on her face. She hadn't noticed him staring at her. The pilot came on the intercom and announced that they were about to depart knocking Winston right out of his gaze." Ok everyone welcome to SouthWest Airlines where we blah,blah,blah. I don't think you guys really care what I have to say, man I don't even care what I have to say. My wife said she's leaving me, I'm going broke. *crying* I don't know what to do anymore. What is the meaning flying If you can't go anywhere?"

The entire plane got silent and everyone was looking around with puzzled faces. Winston turned towards the woman who was as just confused as everyone else on that plane. "I guess someone Is having a really bad day" Winston remarked. "Bad day? This guy shouldn't evencontrol this plane in the state he's in." she commented back. He let a soft giggle escape him lips.

The plane was finally in the air and people were now allowed to get up. Winston unbuckled his seat,and spread his leg to get the feel of his manliness. His knee hit the woman next to him. "Oh I'm sorry,I just got in my zone for a second." Winston said.

" No need to apologize. You're a man, that's what they do; get comfortable."

"At least you understand. You don't get many days to do this."

"Thanks for reminding me, because I think I forget to have some me- time once in a while... Ok all the while."

A small crack appeared on his face. He was enjoying her company. "Um my name is Winston, Winston Bishop." he said sliding his hand to her.

"Well, my name is Ann Perkins,nice to meet you Winston." taking his hand and shaking it. The handshake was quick and the both let go putting their hand to their side. No one said a thing until Ann finally broke the silence. "Soooo where are you from?" a little curious. He turned towards her."I'm from 'The Windy City',Chi-Town,Second City,The Big Onion, Heart of America." Using a deep voice. Ann looked at him with a smirk on her face. Winston closed his eyes and put a hand over his face feeling like a complete fool. " I'm from Chicago and you?'

"I'm from a small little town called Pawnee, Indiana. Not much going on around there."

"Ohhh, you're like them country girls,milk cows, feed the chicken and sheep, and can't hang out with boys or Pa will kill em dead." Winston teased with a southern accent. Ann lightly smacked his arm and started laughing at his silliness. "Nope. That is not me at all a hundred percent that is not me." still laughing. "So why did you leave to come to New York?" asked Winston.

" I got a new job and I really did need to get out of there. Staying in one place most of your life is pretty Borinnng." with a lazy tone.

Winston enjoyed talking to someone instead of listening to a bunch of sad Soul Train music. They were almost talking for an hour now, and the felt like they could go on, and on,and on,and on, well you get the point. "Why did you decide to leave California, Winston?" Ann asked.

"My friend Schmidt, The Douche-Bag I was telling you about got a job opportunity in Florida and my other friends Nick and Jess got married and moved out. Basically the whole loft was mine." Ann looked at him with a frown and rubbed his hand. "Awww it's ok, people do that all the time. They make big steps in their life and move on, but I'm sure they love you Winston. People in my life moved on…..not ready because I moved on, see I'm on this plane right not,moving on. Now that I think of it Jerry moved on because he quit,but he still visited and-." She stopped herself noticing that she was talking too fast. "I'm sorry I can talk a lot." she said quietly.

" Naw it's ok, I can get excited at times too." trying to make her feel better. The Captain came on the intercom once again " Yeah someone just took my burrito. *ugly crying* What else are you going take from me, the wheel". The entire plane full of passenger started shouting "no" and "don't do it man".

"For goodness sake come down people, we will be landing shortly. Now buckle up." said the other pilot.

The planes wheels screeched across the pavement of the ground below them. Everyone seemed relieved and ready to get off that plane. It had finally reached the terminal and people were already unbuckled. "That was some ride right." Ann joked.

"Yeah it was." Winston added.

Getting off the plane everyone went their separate ways."Here's my number if you ever want to meet up and talk or just hang out. I really liked talking to 're really funny". She gave him a slip a paper.

"And It was nice talking to you. Well, I guess we'll meet again." He said with a wide smile.

She turned her heels and walked away. Ann turned around one more time to wave and she was off._"Winston, you did it again"_ he thought. He walked the opposite way. "Yup Mojo Man still got it goin' on." he whispered silently to himself before disappearing into the crowd.


	2. Chapter 2: Small Talk

**Chapter 2: Small Talk**

On Wednesday night in the beautiful city of New York,Winston has only been here for three days and his search to find a place to stay was little to none. Working at the new radio station and doing some little DJ gigs was the only income he was getting. There were many choices to chose from,but they were either too expensive or too old and dirty. Winston was getting about tired and started making his way back to the hotel. It became overbearing having to deal with so much in only the three days that he has been here. Coming to a realization that the walk to the hotel was far he stop by the nearest StarBucks to get a coffee to calm him down and get a little energy before going back out to reality.

Making his way into the Starbucks he went to the end to order his drink. " Uh hello, yeah can I get a Caramel Brulee Latte please." The woman behind the counter asked him what was his name. He told her as she began to start writing his name down on the cup. Winston shifted his body to walk down to the the cashier. Finally reaching the cashier, he dug into his pockets pulling a ten dollar bill out of his wallet. The cashier opened the register, pulling out change and handing it to Winston. Then the cashier handed him his drink and wished him a goodnight.

Winston slowly turned around and caught a familiar face sitting at a table alone with her head in a Fifty Shades of Grey novel. It was Anne, the girl he met on the plane. Winston walked over to the table and stood there in front of her to see if she had ever noticed. Anne must have really been into that book because she didn't look up once. Softly clearing his throat to get her attention she raised her head from that book and looked up. She looked a little curious of who you where and why you were in front of her; that's when a light switched on in her head and greeted him with a smile.

"Oh heeeey you." she said with a half smile. She forgot his name and she made it clear that she forgot. "Winston, and you are Anne I'm guessing?" saying a little hesitant. She nodded her head and slapped her hand to her side and shook her head. _Man I am so weird _thinking to herself. Anne snapped out of her weirdness and motioned him to sit down. Winston pulled a seat out as she slip back into the booth.

"So, how has been New York for you?" Anne asked trying to break the awkward void. Winston cleared his voice before saying anything.

"Not too well. I've been looking all over the city to find a good place to stay, but nothing in price range or standard. Not that I have any." He shook his head and closed his eyes. _This was supposed to be an great time in my life,but it's all going to shabbes. _Anne could she the hurt on his face, the pain that was in his voice. Everyone goes through things in life. Just look at him. There was no way that she could not try and help him. Remembering the last conversation he has exactly no one to turn to for help.

" Hey..uh..listen, there is a space opened at my condo building complex. They are nice, affordable, and clean. I promise you would love it." she said with her hand on her chest. Probably because she was nervous of what he might say next. Winston looked at her wided eyed.

"How much are they because If they are at a reasonable price I'm buying." becoming very interested in what she was saying. He sat up in his seat to give her all of his attention. "About… I don't know… three-hundred thousand." shyly releasing the words out of her mouth. Winston looked down again. That was way too much for the amount he was getting payed. He could barely pay the hotel bill let alone feed himself. He thought he had enough to do this big move,but it was harder than expected. Shifting his body and removing himself from the chair pushing it in.

" You know thanks Anne, but I don't have the money right now. Well, It was nice talking to you. I'm just going to get back to the hotel." He picked up his cup and started towards the door.

" Wait!" a voice called after him. Anne stood up grabbing her book and purse walking towards him. "You need a ride."

They were now in the car trying to get thow heavy New York traffic." Can you believe this is what I have to go through everyday; this is exhausting." saying while honking the horn at a cab thatcut in front of her shapely. Winston looked over to her giving her a little smile. " Everyday? Where do you go everyday to go through this madness if you don't mind me asking?" Winston said. She nodded her head in approval." I'm a nurse here at the Morgan Stanley Children's Hospital of New York. I don't think children like me because everytime I come in the room they kick me and cry like I'm the bad guy. I guess that what I like about my job; it's like I never left home." Winston giggled not sure what to say after that.

"At least their cuteness makes up for all of it." he said jokingly. Anne just sat there at the light with her hands on the wheel at a red light just laughing. Winston couldn't help but laugh about how foolish that sounds. The laughing died down as they sat there in silence. they heard nothing but the honking of horns and low music on the radio. They didn't even know that it was on. The radio announcer was talking and that's when the vibe in the care changed.

"Just a small town girl, livin' in a lonely world

She took the midnight train goin' anywhere

Just a city boy, born and raised in south Detroit

He took the midnight train goin' anywhere…"

Anne turned up the radio singing to the words. she then realizes that she wasn't alone and shuts her mouth in embarrassment. _That when this got real. _Winston opened his mouth, surprising her taking her aback a bit.

"…..A singer in a smokey room

A smell of wine and cheap perfume

For a smile they can share the night

It goes on and on and on and on."

She couldn't hold back much longer and joined in with him to the 80's hit.

"Strangers waiting, up and down the boulevard

Their shadows searching in the night

Streetlights people, living just to find emotion

Hiding, somewhere in the night."

They were rocking their heads back and forth, playing air guitar and drums. She was lost in the moment and it felt so good to let loose for once in a while. People on the left and right were looking out of their windows in disgust like they were some kind of rodent. Anne snapped back into reality when a car behind her honked the horn. She shook her head and fixed her hair. Winston turned the volume down to the radio and looked at her giggling. It was like he never left California.

" Ok let u never do that again...in public." throwing him a little smile. Winston started rubbing his _chin beard or whatever you call that thing on his face._" I make no promises." saying in a devious tone. " Well ok, we'll see if that will work out for you." giving his a smug look.

Anne pulled up in front of the hotel putting it in park. " That was an amazing car ride I must say." Winston shot her a look that no one could explain. He knew that was amazing. For goodness sake he's Winston; that what he is about. He carefully unbuckled his seatbelt, then reaching for the door handle pushing it open. Just as he put a foot out of the car he turned to Anne to Thank her for the ride.

"Hey, It no prob; you are so nice why not do something in return." She made a face after what she said sounded a bit sexual. Winston didn't catch on so she was pulled out of the car saying one last thank you before leaving. That's when Anne shouted out something. " Ummm… Winston, if you still have my number call me and I can see about finding you a place to stay. If that is ok with you of course." finishing her sentence a bit anxious. He bent down to look at her in the car with his hand on the door.

"Yeah that would be great if you could do that for , thank you." Winston didn't know how to express himself. She could tell by the excitement in his voice he was really liking her suggestion. " What time should I call you?" Winston asked. "Ahhh.. about two p.m. if that's fine with you." she said. " Sure, definitely, we'll I don't want to keep you long and nice seeing you again." With that he stood up and shut the car door. He gave a final wave before entering the building.

Anne never thought that she could make friend this fast to her move in New York,but I was nice not feeling alone. Winston does need a friend, so why not. She smiled to herself before driving off. Back out to the busy streets of New York city.


End file.
